Rotating fonts is a straight forward process, so long as the Windows font mapper can supply a rotated font based on the font you request. Note: Using a TrueType font virturally guarantees success. Here is an example of creating a font that is rotated 45 degrees:

procedure TForm .Button Click(Sender: TObject);
var
  lf : TLogFont;
  tf : TFont;
begin
  with Form .Canvas do begin
    Font.Name := 'Arial';
    Font.Size := 24;
    tf := TFont.Create;
    tf.Assign(Font);
    GetObject(tf.Handle, sizeof(lf), @lf);
    lf.lfEscapement := 450;
    lf.lfOrientation := 450;
    tf.Handle := CreateFontIndirect(lf);
    Font.Assign(tf);
    tf.Free;
    TextOut(20, Height div 2, 'Rotated Text!');
  end;
end;